Raising the Stakes

My roommate, Rob, used to work for a small engineering company. When I say small, I mean his boss was the engineer, he was the draftsman and the only other employee was the receptionist. Since the boss was usually out getting the work, that left Rob in the office doing the work. Consequently, he spent a lot of time with the receptionist.

When Rob started telling me about the new receptionist they'd hired, Lisa, I thought things sounded good for him – she seemed to be quite a flirt. Little did I know at the time that hiring Lisa would be beneficial to both of us eventually. Rob would come home and give me the latest each day after work – Lisa did this, Lisa said that – but one day he had even more interesting news. Turns out Lisa is good friends with Dawn, a cocktail waitress at one of our favorite watering holes whom Rob had briefly pursued in the not-too-distant past. I didn't know if this was such a good thing because it looked like things were going well for Rob with Lisa. The last thing he needed was Dawn to distract him and take away his focus – a bird in the hand is worth two in the bush, as they say.

It ended up I was worrying for nothing. If fact, I think Rob may even have had ideas of trying to hook me up with Dawn. The four of us got together for drinks one evening and had a really great time. Dawn and I didn't hook up, but then neither did Rob and Lisa. Instead, we spent the evening laughing and joking like we had been hanging out together for years. We had so much fun that it didn't even bother me that things weren't leaning toward the romantic. That's not to say that I didn't find Dawn, or Lisa for that matter, attractive. On the contrary, I wasted plenty of time daydreaming about what I would love to do to either or both of them.

As time went on, we got together every now and again and always had a great time. Nobody was pushing for anything to go farther, though Rob and I talked about how sweet it could be if it ever happened. One Saturday in December, we finally crossed that line and never looked back.

Lisa and Dawn had come up by us to go Christmas shopping. It was a cold, gray day and after a few hours of going from store to store, we headed back to our apartment to warm up. We made a big batch of hot chocolate and were sitting around listening to music not doing much of anything when Dawn said, "I think this day is trying to put us into a funk. Let's do something fun."

Rob jokingly suggested strip poker.

"We would so whip your butts," Dawn challenged.

This wasn't unlikely – neither Rob nor I was much of a card shark, but they didn't know that. We did know how to keep a poker face, though, and how to get their competitive hackles up. We jawed back and forth about who'd be whipping whose butts until no one dared back down. We broke out the cards, set some ground rules and settled around the table.

It turned out we all pretty much sucked at poker and pretty soon none of us was wearing much. Rob and I still had our jeans and underwear on when Dawn lost her bra. Lisa was already down to just her bikini panties at that point. It was so erotic seeing them gradually shedding their clothes and I had almost blown a load in my pants when I got my first look at Lisa's naked boobs. They were probably 36C's topped with big pink aureola and hard nipples. If the tabletop had been glass they would have seen my rock hard rod straining against the zipper of my Levi's. Of course if the tabletop had been glass, I'd have been able to stare at them in their bikini panties for the past ten minutes and there'd probably be a wet spot on the front of my jeans.

Dawn slipped out of her bra, freeing her lovelies. I'd guess 34C – she was smaller than Lisa, but she was also a smaller girl so they looked nice and big on her small frame.

"So what happens after we get one of you naked?" Rob piped in.

"Rob, you'll be naked long before either of us." Dawn responded confidently.

"Okay, if you're so confident," I said, "how about we make this interesting. If either of you guys wins, Rob and I will both strip off our jeans but..." and here was the interesting part "if one of you loses, you both lose your panties or..."

I trailed off.

"Or what?" they both asked.

"Or you can keep your panties on and Rob and I will still lose our jeans despite winning, but you two have to blow us."

I love playing cards with Dawn because, while she talks a good game, she sure as hell doesn't play one. Lucky for Lisa, it was actually Dawn who lost that hand. Now came decision time. Of course I had to put my two cents in.

"If you lose your panties, the game is over." I explained. "But, if you blow us, you keep your panties, play at least another round and maybe win the next challenge."

This sounded ideal to me because at the rate things were going we'd be seeing them naked at some point soon anyway. I figured why not get some action on the way there. Like two gambling addicts just trying to stay in the game, they went for it.

"But who does who?" Lisa asked.

"You alternate." I answered. I'd really thought this through. "You start on Rob. Dawn starts on me. After a couple of minutes you switch. And whoever blows his load first, the other one gets both of you." I couldn't believe they were actually going for it.

We moved over to the couch and Rob and I slid our jeans off. We both had tent poles in our tighty-whities. Dawn and Lisa knelt before us and slid our briefs down. I think they were both shocked at Rob's size. I'd seen his cock before and I knew that despite his slight build, he was hung. It made Dawn's comment about his "tiny little penis" especially funny.

We both sat down with the girls in front of us. Dawn didn't waste any time. She grabbed the base of my cock in one hand and sunk her mouth down on me. Oh my God was she good! We'd be back playing cards again in no time because there was no way I'd be able to hold out. I watched as my cock slid in and out of her hot little mouth then glanced over at Lisa. She had stretched her mouth around Rob's monster and was working slowly up and down it as far as she could go. Dawn was licking up the underside of my cock and around the head and tonguing my balls before sinking it back into her mouth. I felt the hint of my orgasm starting to build and was just about to say something when Rob said "Switch!"

He must have been getting close, too. He would be in trouble when Dawn got a hold of him. The girls released our cocks and crawled to their new positions. Lisa immediately deep-throated me, I guess since she actually could. Dawn took a second before going to work on Rob with her tongue. I think she needed to prepare before sticking that thing in her mouth. I returned my attention to Lisa, running my fingers through her long brown hair. She was gently fondling my balls while her mouth pumped up and down my shaft.

I could feel her tongue sliding up the underside while her wet, full lips caressed me from root to head. The heat of her mouth intensified the pleasure. The break while they'd switched positions had helped my staying power, but I knew it wouldn't be for long. I really wanted to blow my load in Dawn's mouth, so after just a few minutes I said "Switch!"

The girls switched positions again and I felt the warm comfort of Dawn's mouth immediately. Rob couldn't have had his cock in Lisa's mouth for more than thirty seconds when I heard him grunt. I looked at Lisa trying unsuccessfully to swallow all of Rob's load as it dripped down her chin.

When he finished, she cleaned herself up and moved over next to Dawn. Dawn held my cock, gently pumping, while the two of them took turns sucking and licking it. I closed my eyes and leaned my head back, enjoying what I assumed at the time was a one-time occurrence. I was already extremely close when Lisa joined Dawn, so it didn't take much longer with both of them working on me. When I was about three sucks away from blowing my wad and Dawn took her turn, I put both hands on her head and pushed my hips toward her, indicating that I was ready to blow. I moaned as I shot my load into her hot mouth. Dawn didn't miss a drop and continued to suck me clean until I was totally limp.

We all took a few seconds to recover before Dawn goaded us back to the table with her claims of imminent victory. Rob and I left our jeans behind but pulled our briefs back up – we were all now on equal ground. At the table, I told the girls that Rob and I wanted the same deal they got – if one of us loses, we have the option of losing our last remaining garment or going down on them and keeping it. I figured I'd be a winner even if I lost – I would take eating pussy as a prize or a punishment.

The girls had already lost their option loss, so they'd be losing their panties if they lost, but I had a feeling once they agreed to give us a loss option that I'd be having a terrible hand. Rob may have been playing to win - whether to preserve his pride, to see them naked or to avoid eating pussy – but I was covertly taking a dive. When the hand was over and I was indeed the big loser, I took the "going down" option and Rob reluctantly agreed. I think he figured we'd be going back to the table and he'd be able to win the next hand.

What he didn't realize was that, first, by winning the next hand we'd be stripping them of their panties, which we were just about to do anyway in order to go down on them, and, second, I had no intention of making it back to the table. I was planning to work them over with my tongue then move right along to fucking.

At the couch, I knelt before Dawn and ran my hands up the back of her legs to squeeze her ass before I slid her panties down. Her pussy was incredibly well maintained – her lips were shaved bare and the hair above was closely cropped and groomed. As Dawn sat on the couch, I glanced over at Lisa and saw that her dark bush was a bit fuller. I could feel the blood beginning to return to my organ as I leaned in and spread Dawn's legs. I spread Dawn's pussy lips away from her clit and went to work with my tongue. I slipped one, then two fingers into her dripping pussy and worked them in and out while licking and sucking her clit. She was rotating her hips and holding my head while groaning. The more I licked, sucked and pumped, the longer and louder her moans got and the faster her hips were moving. I was figuring it wouldn't be much longer when I heard Lisa say "Switch!" – I had forgotten about that!

Dawn groaned disappointedly this time when I moved away from her and over to Lisa. Rob took my place between Dawn's legs and I took his between Lisa's. Her bush was indeed fuller, but not overgrown. She kept it trimmed short, but didn't shave as much as Dawn did. I attacked her pussy much the same as I had Dawn's, licking and sucking her clit while fingering her hole. This time she was doing the groaning and Dawn's noises had tapered off. I guess with a tool like his, Rob didn't have all that much practice using his tongue.

Lisa was moving frantically while holding my face against her pussy. I went from flicking her clit with the tip of my tongue to lapping at it with my entire tongue, like it was an ice cream cone, while fingering her faster and harder. I noticed Dawn's moans picking up about the time Lisa arched her back and let out a cry. As her juices washed over my tongue and fingers, Lisa convulsed several times, her body breaking out in a thin sheen of sweat. I let up on her when she relaxed back onto the couch her eyes closed.

I straightened up, kneeling in front of her, and glanced at Dawn. The way she was moving, it looked like she was very close. Her eyes were closed, her hips were pumping and she held Rob's head firmly in place. I looked back at Lisa, who still had her eyes closed, and slipped my briefs down to my knees, allowing my cock to spring free. I grabbed it and rubbed the head up and down Lisa's slit before plunging in. Lisa's eyes flew open, revealing a raging lust in them, and she let out another cry. She reached around to grab my ass, pulling me in as far as she could, and wrapped her legs around me. I started long, slow strokes in and out and leaned down to kiss her. Her hands moved up to the back of my head and we made out.

I broke the kiss only because it was easier stroking when I was upright. I reached out to fondle her big, beautiful breasts and play with her nipples. I noticed that Dawn was moving frantically now, eyes still closed, and groaning louder now. I reached over and fondled one of Dawn's breasts, concentrating on her hardened nipple. Suddenly, she let out a cry, followed quickly by another, as her orgasm tore through her. I released her nipple and returned my attention to Lisa, increasing the pace of my stroking.

I was leaning both hands on the back of the couch and Lisa had her arms and legs around me when Dawn opened her eyes, sucking in her breath when she realized what we were doing, and called out "Switch!"

Nobody complained.

I desperately wanted to fuck Dawn, she clearly was interested in having me, Rob I'm sure was happy to fuck either of them and I'd bet Lisa was thinking about Rob's monster cock. I slipped out of Lisa's slippery channel and moved over to Dawn. Rob was standing in front of Lisa, so she gave him a quick tongue bath before he knelt and slipped into her. As ready and worked up as she was, Rob slipped in pretty easily despite his size, but Lisa still about sucked all of the air out of the room as he filled her up.

I pressed the head of my cock against Dawn's opening, teasing her briefly before slipping all the way in.

I leaned down and Dawn and I shared our first kiss, our tongues snaking into each other's mouths. Her legs were wrapped around me and she threw her arms around my neck as we made out. I was supporting myself with one arm while my free hand played with her breasts and nipples. I suddenly became aware of Lisa making a lot more noise. I glanced over without slowing my pace and saw her thrashing about as Rob reamed her. It sounded like she was having one wicked orgasm.

Having just fucked Lisa myself for a little while, I didn't think I'd be able to hold out very long for Dawn. When I got to a point where I thought I was getting too close, I pulled out and had Dawn turn over. She knelt on the floor and leaned on the couch as I entered her from behind. I sunk myself all the way in and reached around so I could stimulate her clit at the same time – I wanted to make sure she got there, too. I began my long, slow strokes again while gently rubbing her clit and cupping one of her breasts.

I heard Rob begin to grunt and looked over to see his frenzied fucking before he stopped abruptly and collapsed onto Lisa. I picked up my pace, hoping Dawn was getting close. She started getting noisier and pushing back against me to meet my thrusts. I straightened up, releasing her breast and leaving her clit, and grabbed her by the hips and fucked her harder. As I felt that familiar feeling start to build and was worried that I'd beat Dawn to it, she suddenly cried out loudly and I felt her pussy convulsing around my rigid member. I increased my pace even more so my hips were smacking against her beautiful ass. Before she'd finished riding out her wave, I sent shot after shot of cum right up into her.

When I finally finished, I was totally spent. I collapsed onto the floor and pulled Dawn down with me. We lay there recovering while Lisa and Rob did likewise on the couch.

When we had all finally caught our collective breath, we realized we were hungry. We called and ordered some pizza and gave the delivery guy a nice tip by having Dawn and Lisa answer the door naked (had it been a delivery woman, Rob and I would have answered the door). We spent the rest of that day naked, indulging in each other's bodies. We didn't even go to bed that night – we just spread out blankets and pillows on the living room floor and spent the night all together (and believe me, there wasn't much sleeping!).

Sunday didn't end up being the day of rest it's supposed to be, either.